See the LeSS.works site for an overview of LeSS, including for adoptions. Read here for my specific first-step advice.
What are the earliest steps in adopting LeSS? I recommend the following activities and points.
First and foremost, we recommend that the scope of the first LeSS adoption by no more than a medium-sized product group of "50 people." Do not widen the adoption! Keep focused in that 1 group for at least 6 months, and with lots of dedicated expert coaching, both organizational and technical. And in that group, really make the organizational design changes required by LeSS. No "fake Scrum" or "fake LeSS" that is often driven by Larman's Laws of Organizational Behavior.
In this first phrase, we also urge that a group not change to LeSS without the senior management team (both Development and Business) carefully and fully learning first, via the following activities. Without deep understanding, and with the problems of "copying without knowledge," a group can easily end up with a mess or disaster at multiple levels.
I recommend starting with informed consent, and from the start explaining to the people involved in this consent that LeSS is an organizational design change, not a practice or 'method'. And that is why informed consent and deep education amongst a senior management group is critical. And rather than trying to sell or push a LeSS adoption, I encourage a slow, deliberative education process in which the senior management stakeholders carefully and deeply learn the motivations, ideas, and organizational design change implications, all with a focus on why.
The heart of the informed consent phase is the first 5-day visit with me. Some the surrounding activities I recommend include:
1. Readings — A set of particular readings that I advise, to be completed before the week.
2. Familiarity & Preparation Calls — I participate in 1 or more (video) calls with a few key stakeholders, to understand the context, motivation, products, people, and so forth. And to highlight or clarify certain preparation steps.
3. 2-3 Day Course — (week-1) Senior management (and other stakeholders) from both the Development and Business groups join with me in the Certified LeSS Practitioner or Certified LeSS for Executives course.
4. 1 Day Workshop — (week-1) After the course, a 1 day workshop with me to exhaust all senior-management specific questions about the implications, combined with advice on what product group to start with and some starting steps.
5. 1 Day Tech Coaching — (week-1) I spend one day coaching one development team (of 5-10 people) in Legacy TDD via Mob Programming. Why? In addition to the team getting some great technical and perhaps even advanced development coaching, I learn a great deal about the organization by working with the code hands-on, and working with the people and their tools hands-on. This gives me an insight that is very difficult obtain by only talking with senior managers.
6. Slow, Deliberate, Aligned Decision — After I leave (to reduce bias and avoid rushing) the management team slow and deliberately discuss and then decide to go/stop with a first LeSS adoption for one group of "50" people. Combined with this, that the management team develop strong alignment, agreement, and support amongst themselves for this decision.
Next, for the first chosen medium-sized product group, we recommend lots of education for the potential teams, with a focus on why, before "flipping the system." And then we recommend applying volunteering as much as possible, so that the people that will participate in this first group are as much as possible enthusiastic and with energy for the change, rather than prisoners of the change.
Notice that this approach creates a combination of top-down and bottom-up support. That's important for a LeSS adoption.
There are many other adoption principles and steps that we recommend for the first LeSS adoption — and that are covered in the LeSS courses — but these outlined above are the key initial steps.